Imidazole → HCID 178455471, compound

HRID 1873944Notes

Reaction equation

HRID 1873944 reaction equation
Cl.[CH:2]1([C:5]2[C:13]3[C:8](=[CH:9][C:10]([OH:14])=[CH:11][CH:12]=3)[NH:7][N:6]=2)[CH2:4][CH2:3]1.N1C=CN=C1.[CH3:20][C:21]([Si:24](Cl)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([CH3:23])[CH3:22].O>CN(C=O)C>[Si:24]([O:14][C:10]1[CH:9]=[C:8]2[C:13]([C:5]([CH:2]3[CH2:4][CH2:3]3)=[N:6][NH:7]2)=[CH:12][CH:11]=1)([C:21]([CH3:23])([CH3:22])[CH3:20])([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 795Imidazole2×HCID 962WaterHCID 94078tert-Butyldiphenylchlorosilane2×HCID 178479616HCID 178479616, compound

Product 1

HCID 178455471HCID 178455471, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

3-Cyclopropylindazol-6-ol hydrochloride (5.18 g) which can be prepared according to the method described in Reference example 4, etc. and imidazole (4.21 g; manufactured by Tokyo Chemical Industry, Co., Ltd.) were dissolved in dehydrated DMF (122 mL; manufactured by Kanto Chemical Co., Inc.). Then, TBDPSCl (15.67 mL; manufactured by Tokyo Chemical Industry, Co., Ltd.) was added and the mixture was stirred overnight at 20° C. To the reaction solution, imidazole (1.8 g; manufactured by Tokyo Chemical Industry, Co., Ltd.) and TBDPSCl (6.27 mL; manufactured by Tokyo Chemical Industry, Co., Ltd.) were added and the mixture was stirred for 2 hours at 20° C. To the reaction solution, water was added and extraction was carried out twice with ethyl acetate. The organic layer was washed twice with water and once with brine and dried over anhydrous sodium sulfate. After the solvent was evaporated under reduced pressure, the residue was purified by column chromatography (“COLUMN-A”; n-hexane:ethyl acetate=95:5→74:26) to obtain the title compound (4.71 g).

Workup

  1. stirringthe mixture was stirred for 2 hours at 20° C
  2. extractionextraction
  3. washThe organic layer was washed twice with water and once with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter the solvent was evaporated under reduced pressure
  6. customthe residue was purified by column chromatography (“COLUMN-A”; n-hexane:ethyl acetate=95:5→74:26)

Sources & evidence

ORD record
ord-75d989c4b12c45a5ae170a4e0fd900ab
Source dataset
uspto-grants-2012_11
Patent number
US08304443B2

Reaction notes

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